Sleepless Night
by Theeubernoob
Summary: Jaune can't sleep so he decides to get some practice in. Little did he expect to run into Ruby.
1. The Night

It was a chilly night as Jaune made his way to the training complex. He couldn't sleep for the life of him. If he couldn't sleep he may as well get some extra practice in. The sessions with Pyrrha were helping, but he could always use the extra help. Eager to get out of the brisk night, he set a quick pace. He entered the complex, leaving the cold behind Jaune expected to be greeted by silence. This was not the case.

He heard the sound of gunfire coming from one of the training rooms. 'I wonder who that is.' He thought to himself. 'Eh, no harm in checking.' He headed in the direction of the sound, eventually reaching the door. He tried it, finding it unlocked, he pushed it open. What he saw took his breath away. He saw an unmistakable red hooded figure, elegantly flipping through the air, shooting down targets was amazing accuracy. No matter how much he saw it, Jaune couldn't help but me captivated by the ease the red hooded figure fought with. He wanted to call out to her, but he was too enthralled by the girl's performance. An eternity could have passed and Jaune wouldn't have noticed, he was too caught up watching her fly through the air, in a dance as deadly as it was graceful. Not much after that having run out of ammo the red girl landed safely on the floor. After a moment, she finally noticed the blonde boy standing at the door. Giving a quick wave, she pulled off her headphones. "Hey Jaune," she greeted him.

Jaune, finding his voice, managed to return the greeting. "Hey Ruby." An awkward silence followed.

"So..." Ruby started. "What brings you here?"

"Oh, uhh..." Jaune stammered, "I couldn't sleep."

Ruby nodded understandingly. After a pause, seemingly stricken by an idea, she suddenly asks "How long were you watching?"

A startled look crossed Jaune's face, followed swiftly by one of confusion. "Not very long" he started, before stopping to think, "Maybe a few minutes... I have no clue..." he finally admitted. Ruby giggled a little at that. Jaune looked at her incredulously. "Hey!" He retorted. "Your fighting is just really..." He paused, searching for the right word. He wanted to say a lot of things, amazing, beautiful, but he felt he shouldn't, he finally decided on "captivating. Really captivating." 'Smooth save Arc.' Jaune thought, dejectedly. 'She probably thinks your creepy now, sneaking in to watch her.'

Ruby smiled, her usual cheery grin. Another silence fell, more awkward then before. Ruby was the first to break the silence. "Since we're both here anyways wanna spar?" She asked, hopefully. "Pretty please? I'll give you something special if you win." She continued. Jaune had to take a moment to weigh his options. He did come here to practice. And he could spend some time with Ruby. But, even with all the practising he'd put in lately he didn't expect to last five minutes against Ruby, that something special, what ever it was, was probably out of reach. When Ruby eventually decided he was taking too long, she fixed him with an adorable, heart-warming pout. The Ice Queen herself couldn't have withstood this pout. 'Oh not the pout, please stop pouting' Jaune frantically thought. But Ruby would give him no quarter. "Alright," he sighed. Ruby gave him a look of pure elation. 'Well, making her happy will be worth the crushing defeat.' He thought.

Both teens prepared for combat, Ruby having set an automated buzzer to start the battle. 'Alright, think Arc, how should I play this? Defensively I guess. But what about-' the rest of his thought was cut off by the buzzer sounding, and the sudden cloud of rose petals were Ruby once stood. Focusing with all his might Jaune tried to predict the direction of the attack, thinking he had it, he quickly spun around, raising his shield. He was rewarded with the sound of metal clashing, a successful block. 'Alright, all I need to do is keep this up' Jaune thought triumphantly. He managed to fend off the attacks for a few minutes until they started coming less frequently. He was blocking Ruby's fervent attack, and she was starting to wear down. Finally, Ruby charged hoping to feint and catch Jaune off guard, but Jaune was ready. Ruby charged straight on, but at the last second struck from the left, Jaune quickly guarded with his shield before locking his sword into a groove on Crescent Rose and disarming the petite redhead.

As the scythe clattered to the floor Jaune looked on, shocked. He had pulled it off. He had defeated Ruby Rose. The training really was paying off. Jaune was ecstatic, Ruby was one of the best fighters he knew. Pausing in his joy he noticed Ruby. Far from being sad at her loss she seemed genuinely happy. She smiled at him, a warm, friendly smile.

"I promised you something special if you won." She stated. "Close your eyes."

Jaune followed her command, closing his eyes. He felt Ruby move closer "Uh, Ruby?" Any other words he had were snatched away as he felt something warm and soft press against his lips. It only took a second to realize it was Ruby. After a few second she pulled away. Gathering up Crescent Rose, she smiled and said her goodbyes, leaving a very shocked Jaune Arc alone in the room.


	2. The Morning After

Jaune stood shocked. Ruby had kissed him. Ruby Rose, the nice, quirky, and above all else, cute girl, had kissed him. Coming to his senses, he finally spoke, but all he managed was a confused "Huh?" A moment later he managed to call out, but by that time the red teen was long gone.

Jaune reached up to touch his lips, trying to sort out what had just happened. "She kissed me. She kissed ME. Does that mean she likes me?" Jaune continued to stand there, looking confused. Finally he dejectedly sighed, "I'm never getting to sleep now." He decided to do some drills, maybe activity would clear his head.

The morning light brought him no such luck, he was still just as confused. He decided he may as well go change out of his gear, and headed back to team JNPR's room. When he arrived he was found his team awake, more or less, Nora was still trying to wake up Ren. "There you are" Pyrrha called as he entered. "Where were you so early?" After Jaune seemed not to notice Pyrrha continued "Jaune, are you alright?"

Jaune, finally taking notice of his teammate, replied "Oh, yeah, just a bit tired. Did some early exercise today." He didn't feel the need to mention how early. Pyrrha seemed to take his answer quite well. Happy at her leader's initiative, and with Ren finally up, they headed out to get breakfast. They arrived at the cafeteria, and, after getting food, took their usual seats. Not much later team RWBY arrived. Jaune hadn't notice them, he had been caught up in sleepily eating his breakfast. He was oblivious until Yang greeted him with a friendly "Hey Tiger," a hearty punch on the shoulder, and an all too knowing wink. In the time it took him to recover he missed the look Ruby shot Yang, and the halfhearted shrug the blonde responded with. After he recovered, Ruby's smiling face caught his eye.

"So Jaune, did you get any sleep?" Ruby asked sweetly. Pyrrha gave Ruby a confused look, then Jaune an even more worried one.

"Jaune," Pyrrha started "How early was your exercise?"

"Not that early... Okay fairly early... around 1 am..." He answered

"Sounds like a no on sleep." Ruby interjected, after Pyrrha gave her another confused look, Ruby decided to explain. "I couldn't sleep so I went to the training complex, Jaune showed up a little later and we ended up sparring. He won." A faint blush crept up Ruby's face at the final words. At that Yang gave Jaune another all too knowing wink, earning another glare from Ruby. Pyrrha, in her concern for her sleep deprived leader, missed the exchange between the two sisters. Ren on the other hand, did not, he gave Yang a quizzical look, which she replied to with a wink and a sly grin. Ren sighed.

"Is everything alright Jaune?" Pyrrha looked at her leader, concerned.

"Everything's fine, I just can't sleep some times." Jaune hoped that would satisfy Pyrrha, he didn't want to explain the whole reason he couldn't sleep. She accepted his explanation, even if a bit reluctantly.

"Alright." Satisfied for now, she looked to team RWBY, Yang was badgering Ruby over something, Blake's nose was buried in a book, and Weiss looked thoroughly detached from the entire conversation. "You all don't seem very concerned about your leader's sleeping pattern." She gestured to Ruby, who while chipper, was obviously still fairly tired.

Yang gave another halfhearted shrug, Blake didn't look up from the book, and Weiss turned to Pyrrha and calmly said "I just chalk it up to all the sugar." Pyrrha glanced at the younger redhead's breakfast. Ruby had a sugary cereal, chocolate milk, and no less than a dozen cookies. Any further conversation was squashed as Pyrrha's scroll started beeping, signalling it was time to head to class. The group quickly packed up, the two tired captains lagging a bit behind. They all filed to head to their respective classes, Jaune and Ruby following slightly behind. As Yang and Blake turned, Yang gave Jaune yet another all too knowing wink before disappearing from view.

Jaune didn't know what to do, what was he supposed to say to Ruby? Did she like him? She had kissed him after all. Before he knew it, they were at Ruby and Weiss' class. "So" Jaune started before he felt Ruby's lips press against his own. Again he found himself dazed.  
"We'll talk after class" Ruby said, with a sweet smile before heading into her class. Jaune again found himself standing, confused.

A meek "She kissed me," was all he could manage, then he sighed. "Today's gonna be a long day."

**So, here're some authors notes. First off, this chapter took for ever. Been working on it for days, but I kept running into challenges with the whole scene with 8 characters, even if a bunch were passive. Anyways, little information on this: This is a part of my ongoing effort to write more, and more often, as well as to get better at writing in the third person. I hope you enjoy this chapter, and I hope to be adding more on at least a semi regular basis. **


	3. The Next Step

To say Jaune was somewhere else that morning was an understatement. Whether it was because he hadn't slept, or something else Ren didn't know. But one thing he did know was that covering for his spaced out leader was not high on his list of things to do. "Mr Arc, tell me, what was the cause for the Human-Faunus war?" Professor Oobleck asked. Sighing, Ren stealthily whispered the answer to his sleep deprived leader, who repeated it before quietly thanking Ren, then promptly spacing back out. This was going to be a long morning. A flash of gold caught Ren's eye. Yang gave him an impish grin and an all too knowing wink, she knew something. Ren could do nothing but shoot an unamused glare at the mischievous blonde. She in turn stuck her tongue out at him. Clearly she knew something. Sighing again, Ren turned his attention back to what mattered, getting through this damn lecture.

Oobleck's class couldn't have ended sooner for Ren, jabbing Jaune to rouse him, Ren pulled Jaune out of the classroom with him. Clearly something was up, and he knew he'd get nothing from the playful golden teen, so he'd have to ask Jaune. Ren decided to drag him up to the roof, it should be secluded enough up there to talk. He continued to silently drag the blonde knight to the roof, despite his pleading. Finally they reached the roof, and Ren spoke. "What is going on?"

Jaune looked around confused. "You dragged me all the way to the roof to ask what's up? Uh nothing I guess..."

Ren sighed deeply. "Not what's up, what's going on. What's wrong? Why are you so spaced out?" Ren was so done with this day, after classes he was going to sleep and ignore the rest of the day.

Jaune looked a little flustered. "Ruby kissed me."

Ren ran his fingers through his bangs. He was so done with this day, screw the rest of classes, he was going back to the dorm and sleeping. With that thought in mind he turned and headed towards the exit on the roof.

"Wait!" Jaune called after him. He stopped and turned around.

"That's it? That's all of it?" Ren asked. "The girl who obviously likes you kissed you and that's why you're spacing out and acting all weird and confused? Jaune, you're a good friend, but you're dense as a post some times. I'm going back to bed." Ren left it at that, leaving Jaune alone on the roof.

"Sheesh, he sounded annoyed." Jaune turned to see Yang emerge from hiding with Blake in tow. "You really didn't know Ruby has a crush on you?" Jaune hung his head dejectedly. Yang turned to Blake. "He really didn't know. Listen Jaune, Ruby likes you, a lot, and while you're an okay guy, I've still gotta warn you. If you hurt her I'll..." Yang paused a moment before turning back to Blake and making a scissors motion with her finger. "What's the word I'm looking for?"

"Castrate" the black haired teen calmly answered.

"Right. If you hurt her, I'll castrate you." Yang delivered her threat with her usual smile. Jaune gulped at the idea.

"Got it." He stammered out, terrified.

"Good, glad we could talk, bye Jaune, and remember" Yang made the scissor motion again as she left, laughing to Blake as the door close behind them. One again Jaune found himself alone on the roof.

He found himself lost in thought again. Was it really that obvious? Did everyone know Ruby liked him but him? She did always seem happy to see him, and she always tried to sit beside him,and she even shared her cookies with him some times. Had Jaune just been blind this entire time? They'd know each other for months now there's no way he hadn't noticed. But if Ren had noticed, maybe Jaune could have missed it. If Ren noticed it, and he couldn't even notice how much Nora liked him, then everyone probably knew. Jaune really was just that dense.

What Jaune needed now more than anything was some advice. But who could he get it from? His dad? No, he already knew how he would answer "Junior, strength and honour is all a man need to charm a woman!" That wouldn't help here at all. One of the professors? That didn't seem like such a great idea. Ozpin would just look at him funny, and Port would regale him with some ridiculous exploit "Ah, lady troubles my dear boy? I was no stranger to them when I was your age, my problem was there were simply too many! Everywhere I went I had no less than a dozen admirers!" Pyrrha? She'd already done enough to help him lately. Nora? Nora was right out, Jaune doubted he'd get anything more than squeals from the excitable hammer wielder. Team RWBY? He couldn't ask Ruby. He doubted Weiss would even answer. Blake might have some good advice, but if he asked her Yang would know in no time. And Yang was a no go for sure, she'd never give him a straight answer and he wouldn't hear the end of her taunts. Jaune was quickly running out of people. All that was left was Ren. Maybe he'd have some good advice. He was smart after all. Jaune finished class earlier than Ruby anyways, all he had to do was go wake up Ren and ask for some advice. Jaune just had to get through Grimm Studies, and that shouldn't be that hard.

Class passed surprisingly easily. There were no live combat demonstrations, and minimal teaching, Port seemed too caught up in his self glorifying story to spend much time teaching. As class ended, Jaune rushed off to the dorms. There he found Ren, laying on his bed. "RenyougottahelpmeI'msupposedtomeetRubyinanhourandIdidn'tknowshelikedmeandeveryoneknew!" Jaune exclaimed in one breath. Ren sat up, looked at Jaune and blinked, before sighing.

"Jaune, you're over complicating this, just go and talk to her, it's simple."

"I guess you're right. Hey, I've got a question. Did you know Nora likes you or am I the only dense one?"

"You're the only dense one. And before you ask, no it's not as simple as your situation." Jaune wanted to ask, but Ren had gone back to laying down with his eyes closed.

Jaune decided to leave Ren be and go and wait for Ruby to finish class.

He didn't wait very long before seeing Ruby, as soon as she saw him, she gave a happy wave and bounded over. They started walking, no where in particular.

"So" Ruby started this time she was the one silenced by lips pressing against hers. As Jaune pulled away, he saw Ruby smiling.

"Want to get dinner tomorrow?" Jaune asked.

Ruby nodded in response, then standing at her tallest she kissed the blonde again, before saying her goodbyes and running off. Jaune could get used to kissing Ruby.

**AN: This chapter ended up being really quick to write, so woot. It'll take a bit longer to get chapter 4 out, but hopefully I'll have it done before Saturday. Thanks to everyone who's reading this and encouraging me to continue. I hope to make next chapter even longer, so keep your eyes open, for another update soon, next up: the first date.**


	4. The First Date

**AN: Well, this chapter took longer than I expected. I ended up being busier than I thought. But anyways, without further ado, The First Date:**

Jaune was as excited as he was nervous. It was only an hour until his date with Ruby. Jaune couldn't help but worry. What if it all went wrong? What if when they spent time together, alone, in a romantic setting, she realized didn't really like him?

"Jaune? Is everything all right? You've been pacing for past half hour." Pyrrha looked worried for her leader.

"Of course it is. I'm just nervous. Really really nervous." Jaune stopped pacing

"It's nothing to be that nervous about, first dates can be a challenge but they're like any other date. Obviously you've-" Pyrrha's train of thought was stopped as she saw the look on Jaune's face. "You've never been on a date." Any further conversation was halted by a loud knock on the door. Nervously Jaune opened it, and in stepped Yang.

"You're wearing that?" Jaune was just in his every day clothes. "What ever, I just came over to tell you, if you try anything funny tonight, I'll make you wish I just castrated you." She made a crushing motion with her hands, and after giving the rest of team JNPR a happy smile, the golden teen left.

"She does have a point." Pyrrha said. "You should dress a little nicer for a first date."

No sooner had the words left the redhead's mouth when Nora jumped up. "Ooh! Ooh! I'll do it!" and with that she started to dig through Jaune's clothes until she made a full outfit. She then grabbed the blonde knight by the collar and dragged him to the bathroom. After a couple minutes of struggling Nora opened the door to show off her work. Jaune instead of his usual outfit, was wearing dark jeans, a light grey dress shirt, and a black vest. For the rest of the time before the date team JNPR tried to calm the nervous blonde with advice about dates. After getting some all too brief advice, it was time for the date.

Jaune crossed the hall and knocked on team RWBY's door, he wasn't surprised to have it answered by Yang.

"Ruby's just finishing up getting ready. Don't worry, I've already threatened you plenty, I know even you wouldn't be dumb enough to try anything." Jaune was relieved to hear that, a little insulted, but relieved. As he was about to reply the door opened again and Jaune found himself suddenly at a loss for words. Ruby stood there, and instead of her usual ensemble she was wearing a simple yet elegant red dress and had a small red bow in her hair.

"Wow Ruby you look..." Jaune was at a loss, beautiful didn't cut it. 'Indescribable? No that's too cliche. Radiant? Isn't that how you describe pregnant women? Yang might kill me if I said that. Alluring? Yang would definitely kill me if I said that. Gorgeous?'

"Jaune?" Jaune realized he'd been standing there trying to think of a word for well over a minute.

"You look beautiful." Ruby smiled, and the two started walking to the airship dock to catch the airship to town.

From behind they heard Yang call "Have her back before eleven!" As the pair rounded the corner out of view, Yang turned to her faunus partner. "My baby sister's growing up." With that, the golden teen went back inside.

The flight didn't take too long, but it was too long for Jaune. Air travel and Jaune did not mix. They decided to take a walk around Vale for a bit, to settle the blonde's stomach before they ate. The date so far had been mostly silent, a very awkward silence. Neither hunter-to-be seemed to know what to say, and the longer it went, the worse it got. 'This is going terribly. Come on think Arc! What can we talk about? What does Ruby like? She likes weapons, sweets, red things, Aha! That's it!'

"Hey Ruby, wait right here, I'll be right back." Jaune ran ahead to a cart not too far up the road.

"Jaune?" Ruby called after him, but remained in place. She could see him buying something, then returning with something hidden behind him. "Jaune? What've you got there?" The blonde knight pulled out a flower, more specifically a rose, and tucked it behind Ruby's ear.

"I saw the flower cart and figured you're Ruby Rose so I thought maybe I'd get you a rose. I know, it's super cheesy and-" Jaune's explanation was cut short as Ruby stood at her tallest and kissed him on the cheek. Blushing, she gave him a heartwarming smile.

"Thanks Jaune, I love it." It was Jaune's turn to blush this time. Jaune's plan ended up working, the two awkward teens found it easier to talk, and the more they talked the easier it became. With Jaune's stomach settled and the silence abated, the pair made their way to a nearby restaurant.

The restaurant was a fairly casual place and the pair were quickly seated. They ordered their drinks, Jaune a rootbeer, and Ruby a strawberry milkshake.

"I'm surprised." Jaune said, Ruby looked at him, confused. "You got a strawberry milkshake, I would've thought you'd want chocolate. You're always inhaling chocolate chip cookies."

Ruby smiled at him. "Nope. I prefer strawberries, there just aren't many good strawberry cookies. I've always liked strawberries. When Yang and me were kids she'd get mad at me sometimes and when she did she'd eat all the strawberries. Sometimes she'd just put them where I couldn't reach them. She stopped doing that after I fell off a chair trying to grab them. She found me on the floor when it happened, I was crying because I'd hurt myself. She just reached up and grabbed the strawberries, handed me them and patted me on the head."

"Having a sibling must be nice. You and Yang seem really close. When I was a kid I always wished I had a brother. An older cooler brother, someone I could get advice from. All my dad's advice always came down to was confidence, honour, strength or tenacity. Just stuff like 'There is nothing a tenacious man cannot do Jaune!' or 'There is no battle an honourable man cannot win!'"

Ruby laughed at the advice. "He sounds like quite a character."

Jaune smiled, Ruby's laugh was the most beautiful he'd ever heard. "I guess he is, I remember this one time..." The pair continued to talk and swap stories as they ate, and before they knew it, hours had passed and it was 10 already.

"Time flies, huh?" Ruby said as they walked through the warm night. The cold of their last nighttime encounter had given way to warmer weather.

Jaune smiled. "Yeah. I had fun, we should do this again."

Ruby nodded. "Me too." Ruby paused, thinking about something. "So does this make us a couple?"

"I guess it does." At that Ruby grabbed Jaune's hand and the two walked back to the airship dock, a happy couple.

**AN: So again, sorry this was later than I hoped. But as always, hope you enjoyed it. Any and all feedback is appreciated, and I'm always happy to answer any questions. I hope to get the next chapter done in the next two days so keep an eye open.**


	5. The Time Between

**Hey guys and gals sorry for this taking a week, this chapter is going to be a bit different. Last chapter was the end of that arc. I have a plan for the next stage, but to get there I need to skip a couple or three months, but I don't want to leave out all the little things that would happen. So this chapter will be a few shorter stories talking place between the first date and the next stage of the story. Hope you enjoy it. I'd also like to thank everyone supporting this, I really appreciate it.**

Ruby wasn't happy. She had other things to besides sitting in a stuffy library reading a fifty year old book on scythe wielding. It was a beautiful day out, she wanted to spend the day outside. And worse still The Ice Queen herself was holding all Ruby's sweets hostage until she finished reading the books and taking notes on them. Ruby let out a defeated sigh and let her head hit the books. It would have been tolerable if she at least had Jaune to keep her company, but Weiss 'expressively forbade' that, saying Jaune was 'a distraction.' Ruby heard footsteps approaching and prepared to explain herself to her teammate. Ruby didn't expect a certain knight to enter her view. "Not going well then?" He asked with a goofy smile.

"Jaune what're you doing here! If Weiss catches you she'll be really really angry and she'll be really really scary." Ruby was a little panicked at the prospect of Weiss catching her, Jaune didn't seem to take any heed though. He looked around, scanning the area, after deciding it coast was clear he pulled out a small paper bag, and as stealthily as he could managed place it on the table. Ruby took a peek in the bag and couldn't help but smile. She gave the blonde a hug and a quick kiss. "Thanks for the cookies, you're the best boyfriend ever." Jaune smiled, and fearing the wrath of the Ice Queen, bid a quick farewell. Ruby took a big bite of a cookie, maybe the work wouldn't be so bad.

Jaune and Ruby had just gotten back from a successful date. They hadn't been dating for long, but it was going quite well. They stood in the hallway between their respective rooms sharing their goodbyes. Given how well things had been going, the pair seemed oddly tense. Jaune moved for the usual goodnight kiss, as their lips met something changed. This kiss was like none they had shared before, it was full of a carnal passion, their tension seemed to further this kiss. The kiss clawed at them until they could hold out no longer, breaking apart to breathe. Ruby could stand no more. "Take me Jaune, right here in the hallway!" She exclaimed throwing off her cloak.

The door burst upon and Yang quickly stepped through it. She found herself facing her rather startled sister, and said sister's terrified boyfriend. The two stood frozen, Jaune's arm outstretched, holding a calendar, and Ruby pointing to a spot on it. "Hey sis." Ruby managed to say. "Need anything?"

Yang looked a little startled, but managed to recover. "Hey Ruby, Jaune. Nevermind." And as quickly as she appeared, she disappeared back into the room closing the door.

Ruby shrugged to Jaune. "So Monday, Friday and statuary don't work, Why not Wednesday?" Jaune nodded, still stunned by Yang's outburst. "Anyways night Jaune, I'll see you tomorrow." The pair shared a quick kiss before retiring to their beds for well needed rest.

It was past 11. Yang had made it very clear to Jaune that Ruby was to be back before 11. No ifs, no ands, and no buts. She was going to find those two and give Jaune a piece of her mind. And a few bruises. But where would they be? She could ask JNPR, they might know. Yang quickly crossed the hall and knocked rather loudly on the door. The door opened to reveal Pyrrha. "Hey Pyrrha, do you happen to know where your leader is, I need to hurt him." She delivered, as chipper as always.

"With Ruby I assume. I believe they were in the common area. Why do you-" Before Pyrrha could even finish Yang had rushed off to find the pair, giving Pyrrha a wave and a quick thanks.

Yang stomped into the room, ready to lay the pain on Jaune, only to be stopped in her tracks by the sight that greeted her. Ruby and Jaune had fallen asleep cuddled together on a couch, their homework splayed out in front of them. As much as she had to be the protective sister, Yang had to admit the two made a cute couple. The lecture could wait until tomorrow, the pair looked too cute to wake up.  
Yang sighed as she stalked her way out of the room, careful not to wake them. It was then that Yang noticed her partner had followed her and was smirking at her. Yang gave her best glare before smiling at her partner.

As far as lunches went this was the most average lunch ever. Blake read while Yang pestered her, Nora recounted a story while Ren corrected her, Pyrrha and Weiss talked about schoolwork, and Jaune and Ruby were wrapped up in Nora's story. Nora was thrilling the couple with one of her weird dreams, as usual Ren featured prominently in the dream. While she found the telling interesting, Ruby had to wonder, the pair had been friends for ever, and Nora clearly liked Ren, Ren seemed to like her back. So why? Why weren't the two dating? Ruby had been dating Jaune for three months now and she really liked it, it made her feel happy in a way she'd never felt before. If Ren and Norra dated they could feel that same happiness. In her mind there was no reason the odd pair of childhood friends shouldn't date, but clearly there was something. Ruby decided she would ask the pair. Not long after, Nora triumphantly finished her story, and Jaune began clapping. Ruby asked the question. "I've been wondering, why aren't you two dating?" Ren inhaled his soup in surprise, immediately starting a coughing fit. Nora suddenly jumped up as if something had caught her attention.

"Oh no! I forgot my homework back in the dorm!" She lied, badly, before rushing off. Ren, as calmly as one can while coughing, excused himself to get a drink, heading in the opposite direction. A few minutes passed before it was clear neither intended to return to the table that lunch. After that Ruby was certain something was up, and she decided that she was the one to get to the bottom of it. But she couldn't do it alone. A thought flashed through her mind. She had the perfect helper. She turned to Jaune and gave him an innocent smile. He would be the prefect help.

**Up Next: The Matchmaker**


	6. The Match Maker

**Hey guys and gals, Theeubernoob here. It's been about four weeks, and I'm sorry, life happened and I didn't have much time or drive to write, I intended to make this chapter longer to make up for that, but no telling how long it'd take me given how things have gone, Thanks everyone for being patient. And as I can't figure out how to get linebreaks to work, italics will show you when I've jumped around. Hopefully that should work. Anyways hope it's worth the wait, and I'm always happy to hear from anyone about the story, so don't hesitate to drop me a message.**

_It_ had been a few days since the awkward lunch and things were going strangely. Ren and Nora were actively avoiding Ruby, but weirder still the chipper redhead didn't seem to mind. She seemed oddly distant, as if she wasn't entirely there. When ever anyone asked Ruby what was happening she would shrug them off. Her teammates had had enough of it, and nabbed Jaune to all have a talk with Ruby. They were in the dorm, preparing to find Ruby when suddenly she burst through the door.

"I've got it!" she yelled, throwing the door closed behind her. "The perfect plan! Oh hey Jaune." She gave her confused boyfriend a quick hug. Not giving any of her confused friends any time to respond, she continued. "I've got the perfect plan to set up Ren and Nora!" She exclaimed, only to be met with blank faces. Yang's expression quickly changed to one of annoyance.

"That's it? You were planning?! Ruby, we were worried sick about you! You were acting all weird and distant and we were worried about you!"

Realization dawned on the excitable girl. "Ohh... Sorry about that." She giggled.

Yang sighed. "Why are you even trying to set Ren and Nora up anyways?"

"They clearly like each other, and dating Jaune makes me happy, so I figured maybe dating would make them happy. Plus they'd just look so cute together."

They all agreed, but no one expected who spoke up next. "So what's this plan?" Weiss asked, calmly. "Don't look at me like that, Ruby is right, they would look cute together."

Ruby smiled, "Well we're going to trick them into going on a double date. But the problem is they're avoiding me, so..." Ruby recounted her surprisingly well thought out plan to her friends. After it all they set out to work, the date would be tomorrow.

Thefirst step was the easiest, getting Pyrrha to their side. The Spartan was always willing to help, and like everyone else, probably thought the two would make an adorable couple. Jaune sent her an urgent message, saying to head to Team RWBY's dorm. Pyrrha quickly responded, rushing to the room, slightly worried. She arrived, was greeted by the younger redhead, and quickly ushered in the room. The scythe-wielding redhead quickly explained her plan to the redheaded Spartan, the latter quickly deciding to go along with it. And so the match making plan began.

_Jaune _wasn't sure this was such a great idea. It didn't seem that nice to try and control his friend's love life. Ren and Nora had left him and Ruby alone to figure things out. Sure it wasn't the same, Ren said it himself, it was more complicated. But at the same time there was clearly something keeping the pair apart, and they both either couldn't or wouldn't work their way through the problem. But could he just play with his friends' lives like that? No. No he couldn't. He could help his friends though. He wouldn't go behind their back with Ruby's plan, he'd go and talk to Ren.

The group had all been dismissed to prepare for tomorrow, Jaune had the perfect chance to talk to Ren. "Hey Ren, Oobleck's assignment is confusing me, can you give me some help?" Ren nodded. "Somewhere quiet." Jaune quickly added, motioning to Nora, who was busy jumping around and generally being loud. Ren nodded again, understandingly.

The pair made their way to the library, chatting about the assignment. They arrived quickly enough and settled down at a secluded table. They worked for a while, Ren aiding Jaune, and Jaune being overall distant. Admittedly he was actually confused about the assignment, but he was trying to figure out how to broach the topic. He heard Ren sigh.

"What's wrong? Clearly this isn't just about the assignment."

Jaune decided quick was best, like ripping off a band-aid. "Why aren't you and Nora dating?" Ren made to leave before Jaune stopped him and explained. "Ruby has this really elaborate plan to try and hook you and Nora up and I wanted to talk to you." Ren sat back down. He looked a little annoyed at the whole thing.

He sighed deeply. "I've known Nora sixteen years. We've been friends since before we could carry a conversation. We've been through everything together, good and bad, and I love her. But I can't help but worry. What if we try it and it all goes wrong?" Ren looked anything but his usual composed self.

"I think it's my turn to give you some advice. Go for it. You love her, she loves you, it'll work out." Jaune smiled reassuringly. Ren seemed to regain some of his composure, and shot a smile back. "Oh, I guess I should tell you, I'm supposed to trick you into a double date tomorrow, so just act surprised."

Ren sighed, but nodded. It was a little annoying having someone playing with his love life, but it seemed like it would be fine. The pair, having finished with the topic, went back to work on the assignment. They eventually return to the dorm for the night.

But something kept Jaune up. He after that talk of love he couldn't help but think, was he in love with Ruby?. Clearly he liked Ruby, he liked talking with her, just sitting with her, reading, eating, cuddling, almost anything with her. He liked her laugh, her smile, even her cute little snores, he liked everything about her. He wanted to see her safe and happy, and all of that. After all his thinking, as he drifted off to sleep, one thing was clear. Jaune Arc loved Ruby Rose.

**Up Next: The Plan**


	7. The Plan

"The plan is simple. First Jaune needs to distract Ren and get him out of JNPR's room."

"_Hey _Ren, can I get some help on Port's essay?" Jaune asked as classes ended.

Ren nodded. "Yeah, we'll work in the library. It should be quiet there."

"_Second_ Pyrrha will bring Nora to the training annex for sparring, where they'll conveniently run into team RWBY."

"Isn't Nora avoiding you though?"

"Don't worry, I've planned for that. Yang, you may have to take one for the team. If we distract Nora she'll forget all about avoiding me, so you're gonna have to spar with her."

"_And_ then I punched the deathstalker into the other deathstalker and got to keep all the syrup."

"Nora, I thought this story was about Ursa." Pyrrha stated, exasperated. The Spartan was glad they would soon be at the annex, she could only stand so much Nora at a time.

Luckily for Pyrrha the pair arrived in good time. She steered Nora to the room she knew team RWBY would be occupying, and was soon greeted by the sight of the four huntresses-to-be warming up for their supposed team exorcizes. Ruby waved, then beckoned the pair over. Nora seemed apprehensive, so Pyrrha urged her along while heading over to their friends herself. They exchanged greetings before Weiss spoke up.

"So Pyrrha, I could benefit from sparring with someone different from usual, would you mind?"

"Not at all." The two went off to one side of the room and begun sparring. The trap was set.

Nora fidgeted, clearly wanting to spar. The more she watched Pyrrha and Weiss battle, the more she wanted to spar herself. When it seemed Nora could take it no longer, Ruby signalled Yang. The bait was placed.

"Nora, are you okay?" Yang asked. The response was incoherent as Nora exclaimed something faster than anyone could understand, and grabbed Yang, dragging her off.

"You. Me. Spar." Nora managed to get out, readying Magnhild. Annoyed at having to fight a hyped up Nora, but understanding it was for the greater good, Yang readied Ember Celica and adopted her fighting stance.

The fight started with a bang, Nora firing a grenade. Yang quickly dodged past it, aiming a jab at the redhead. She had to dodge away last minute, as Nora brought Magnhild to bear with a powerful swing. Yang charged back in, uppercutting the hammer-wielder before she could recover. The punch connected, pushing Nora back. Sooner than Yang expected, Nora recovered and returned with her own charge, catching the blonde of guard, and knocking her back. The brawler adjusted quickly, firing backwards to propel herself back towards the hammer-wielder, winding up a powerful right hook. Yang collided with all her might, a hard hit, but Nora would give no quarter. She dug in, and brought Magnhild down with all her surprising might. Yang was floored, literally. Before the blonde could rise, Nora shifted her weapon into grenade launcher form, and levelled it on Yang.

"I win!" She gleefully exclaimed, eliciting a groan from Yang. As Yang limped away, shooting Ruby a death glare, Nora continued. "Again!" She chanted. Ruby smiled and approached, volunteering to face the excitable girl. Nora accepted, readying herself again. She was winded from her last fight, but still able to keep going.

Ruby smiled to herself. Her plan was going great so far. Nora was so excited she had forgotten all about avoiding Ruby. Now all the petite redhead needed to do was face Nora herself. More action would distract her more. It had been Weiss' idea. Ruby's just had Yang distracting Nora, but Weiss advised Ruby made sure Nora was truly distracted by facing her herself. But Ruby had a plan for facing Nora. Mostly. It was more an idea than a plan, but she believed if she could keep avoiding, she could tire out her already winded foe.

A buzzer startled Ruby out of her thoughts, the round had begun. As quick as a shot, Ruby fired Crescent Rose, and disappeared in a cloud of petals. Nora responded by firing a grenade at where the younger girl had been standing. As Ruby was no longer there, Nora decided the next course of action was to spin and find where she had disappeared to. Ruby did her best to avoid being spotted, but was caught unaware as Nora suddenly spun around and fired a grenade. Ruby fired to propel herself away form the blast, and decided avoidance wasn't going to work, a change of tactics was called for. 'Nora has power on her side, but she lacks defence. If I hit quick enough, I should be able to avoid her attacks.' Ruby thought. Ruby charged, slicing past Nora before she could swing back. Unfazed by Ruby's new assault, Nora began to blind fire grenades. Lobbing them wherever the reaper might be. Ruby proved an elusive foe, using her semblance and scythe to avoid the explosions. When Nora stopped to reload, Ruby took her chance for a last ditch charge to end the match. She swung her scythe back, and was met with an empty click. Her clip was empty, as quickly as she could manage, she reached for another, but equally as quickly realized she hadn't packed a spare clip. Nora was looking similarly panicked. In the end the pair decided to call it a draw. Ruby didn't mind though, everything had worked out.

"That was fun. But I'm starving. Ooh! We should go get to a restaurant!" Ruby happily exclaimed. Nora happily agreed. The trap had been sprung, and it had worked. The rest of the group all declined the offer. Leaving Ruby to bring Nora to the location of the set up double date.

_The _pair walked into the restaurant, Ruby caught sight of Jaune and steered Nora over to the table where Jaune sat waiting with Ren. Ruby sat down opposite Jaune. Confused Nora sat down opposite Ren.

"Ruby, what are Ren and Jaune doing here?" Nora asked.

Ren answered before Ruby could. "It's a double date. They set us up on a double date." He then bashfully added, "I think we should try it."

Nora smiled at her childhood friend. "Okay."

**Hey guys and gals. Things were a bit hectic this past week with classes starting back up, but I should be able to find more time to write from here on out. So should be a shorter wait for next chapter. Hope you liked it.**

**Up Next: The Double Date**


	8. The Double Date

**Theeubernoob here, this is closer to the update schedule I hope to be keeping from here on, every two or three days. So here's Chapter 8, The Double Date. Hope you like it. And again, thanks to everyone who reads and reviews, you guys and gals are the best.**

So far the plan had worked insofar as it had gotten Ren and Nora on a date. That was a huge success. But now that everything had fallen into place Ruby had run out of plan. She planned up to the first date, but with no experience with double dates the pan cut off. She was left trying to work it out on the fly to help ensure the date went as well as possible. The plan had worked great, there was no denying that, but the date, well the date was something else all together. It wasn't that it was failing. It wasn't even that it was awkward like Ruby and Jaune's first date had been. It was that the double part of it didn't seem to be working. Try as they might not to, Ruby and Jaune were stifling Ren and Nora's first date. It started with Ruby trying her hardest to keep the conversation going, sometimes to the detriment of the conversation. When things seemed to be getting awkward to, she would abruptly change the course of the conversation, unfortunately, being quite awkward herself, on more than one occasion Ruby halted the conversation on a false alarm. The more it went on, the more awkward worry of Ruby's rubbed off on Jaune. He had started the date calm, but as it progressed and the forming tension built, he grew nervous and fidgetty. By this time he had already dropped no less than four forks, and knocked over three glasses of water. His nerves were beginning to show on his face as he thought about the next move.

'Oh man, we're killing their date. Quick Arc! Think of something!' He thought to himself, quite panicked. 'Alright we can save this. I just need a plan. Come on Arc! You can do this! You know you can! ... Dammit I can't do this.'

"Jaune? Are you Okay?" He heard Ren ask.

"Oh uh... Bathroom!" He managed to exclaim, sprinting away from the table.

"I've got to use the bathroom too!" Ruby almost shouted, jumping up from her seat, and disappearing in a cloud of roses.

The two met outside the bathrooms, they had to figure out what to do. "This is going terrible!" Ruby cried. "What should we do!" Both paused to think, before locking eyes.

"We need to get out of here!" The both exclaimed, rushing off to entrance, quickly shoving a few notes into a waiter's hand, blurting their table number, and fleeing out into the evening. And thus, the double date became a single.

_Ren_ had a good view of the door, and was surprised when he suddenly saw his friends, sprinting out of it. "What the..." He started, but decided not to finish. He wouldn't draw Nora's attention to their fleeing friends. As good of friends the awkward couple were, they could be quite awkward, and were both clearly more nervous about this date than either Nora or himself. They likely had the best intentions.

As nice as the restaurant was, a change of venue would be required to keep his date ignorant of their friends' flight. They would likely make a beeline for the airship, so the shopping district would be a perfect location.

"Hey Nora, Ruby and Jaune already said they'd foot the bill, so want to get out of here? Things are a little tense here."

"But shouldn't we tell them? It wouldn't be nice to skip out."

"It's ripping off a band-aid, it will be painful either way, so you may as well do it when they're not paying attention." Ren had to admit it was a weak argument, but logic wasn't Nora's strong suit, so he should be safe.

"Okay." Nora didn't seem to like the idea too much, Ren wouldn't have like it either if he hadn't seen them flee. Ren didn't much want to deceive Nora, but she could be impulsive so it was better to err on the side of caution. He quickly led her outside.

"So where're we going?"

_It_ hadn't been a particularly dignified escape, but the awkward couple pulled it off. They worked their way to the airship dock. Jaune could hear half a conversation as Ruby explained what had happened, and tried to offer the rest of Team RWBY and Pyrrha a defence of their actions. From the look on Ruby's face it wasn't going too well. Jaune knew it was about time to intervene, Ruby was starting to look like a scolded puppy. He tapped Ruby on the shoulder to draw her attention, and mimed for her to hand him the scroll. She did, looking a little confused.

"Things were fine between them, but we were awkwarding it up, we had to get out of there." He stated before ending the call. "That should do." He said to petite scythe-wielder. The blonde knight handed her back the scroll, not surprised when she kissed him.

"My hero." Ruby said, a bit sarcastically. The pair laughed.

"So how much do you think Yang's going to kill me for that?"

"Just a little bit."

_The _other half of the double date wound their way through the evening crowds in the shopping district. They had already been wandering for a little while. They had stopped in a few shops, mainly to browse. The sweet shop was one notable exception, Nora had demanded they go there, and had begged Ren to buy her some. The pair found it easy to talk and were having a good time of things. All in all things were going well. But one thought couldn't help but find its way into both of them. Dating didn't seem any different to their usual outings. Ren decided to steer them to a park or somewhere else they could sit down. He found a small park not far away, and took a seat on a bench, motioning for Nora to do the same.

"It doesn't really seem all that different, does it?" He asked, not expecting any real answer. Nora nodded. "I guess it wasn't worth worrying about after all." Nora laughed at that.

"You worried about us going on a date? That sounds a little silly."

"It wasn't really the date I worried about, but it changing everything. I guess it is a little silly."

"Yeah, it hasn't really changed anything, except that I can do this!" As she exclaimed that she leaned over and planted a kiss right on Ren's mouth.

Ren was surprised, pleased, but surprised. Unsurprisingly, Nora tasted sweet. Ren had to admit that as apprehensive as he had been to taking this step, it felt right. After a moment Nora ended this kiss.

"So we're together together now." She half asked. "Right?"

Ren smiled. "Yeah. Together together." He'd have to thank Ruby when they got back. After all she had orchestrated this whole date. But that could wait until they got back. For now, he was still on a date. "Come on, let's go get ice cream."

_Jaune_ and Ruby sat on a bench. They had made it back to Beacon and were resting in the grounds while Jaune recovered from his air sickness.

"I hope things are going well." The red teen said.

"I'm sure it's fine." Jaune responded.

Ruby was a little worried, Jaune had been unusually quiet the ride back. Even factoring for his air sickness. She had to wonder what was on his mind. Seeing no better way she decided to ask. "What's on your mind?"

"Huh?" Jaune replied, a bit confused.

"You've been really quiet."

"Oh. I was just thinking."

"What about?"

Jaune looked around him, the grounds of Beacon were a sight to behold, even at night. But to him the lushest grounds paled to the beauty of the girl sitting beside him. Things hadn't gone very well that night, but he felt he had to tell her.

"I've been thinking about us. It's nothing bad. I know that's what you say when you're about to say something bad but I'm not so don't worry."

"Jaune."

"Yes?"

"You're rambling, is everything alright?"

"Better than alright. I've been thinking and I've figured something out. Ruby Rose, I love you."


	9. The Aftermath

"He what?"

"You what!"

"He told me he loves me."

"I told Ruby I love her."

Yang was reeling. Ruby had suddenly arrived in the dorm, looking shocked. Yang had been ready to tease her sister about the double date, but the sight of Ruby had stopped her plans immediately.

"So what did you say?" Yang pressed. This was big.

"I... Uhh..." Ruby started, before stopping, trying to find the right words.

Across the hall a similar conversation was happening between Jaune and Pyrrha.

"What did she say?" Pyrrha was excited, Nora and Ren on a date and Jaune professing his love for Ruby both on one day? It was almost too much romance to bear.

"She... blurted something I didn't catch and ran." Jaune sighed, flopping down on his bed.

"Oh. Well then." The excitement was killed. "She's just across the hall, you should go talk to her."

"I doubt he really wants to see me." Ruby dejectedly said to Yang. "I didn't just run, I sort of panickedsomuchIusedmysemblance."

"Ruby," Yang sat down on her bed beside he sister, affectionately placing her arm around her. Sometimes Yang could be mistaken Ruby's mother, she could transition to supportive mode so well. "I'm sure Jaune understands this is all a big misunderstanding. Sometimes people just panic."

"I don't know what to think." Jaune said, though he had been speaking to Pyrrha, he said this to no one in particular. A statement to no one, or perhaps to himself. Not wanting to dwell much longer on it he shrugged off his armour plates. "I'm just going to bed." At that he pulled his pillow over his head, shutting out Pyrrha. Sleep didn't come to him as quick as he hoped, but still beset him soon enough.

Pyrrha sighed deeply. She doubted there was anything else she could do tonight, she would talk to Yang in the morning. The blonde brawler would know more about how to proceed.

_The_ following morning happened to be Saturday, so there were no classes. Jaune stayed in the dorm, saying he wasn't feeling well. When his teammates had offered to stay with him, he had ordered them to go and get breakfast. When they reached the cafeteria they saw team RWBY, minus Ruby herself, in their usual spot. They quickly got their food and sat down at the table.

"Good morning." Pyrrha greeted the others. "Where's Ruby?"

"She wasn't feeling well. Same thing for Jaune?" Yang asked, giving Pyrrha a knowing look.

"Yes, he was feeling under the weather." Pyrrha replied, including a knowing look of her own. Yang's only reply was a muted sigh. The rest of the meal passed fairly normally. Ren and Nora told the rest about their date, in truth it was mainly Nora. Blake and Weiss had been out when Ruby returned, having grown bored of waiting, they had both left to find quiet spaces, Weiss to work, Blake to read. Pyrrha hadn't thought it kind to spoil the mood of the new couple by telling them. As none of them knew, the mood at breakfast was lighter for the four than it was for Yang or Pyrrha. Both were lost in thought for most of the meal. The situation had quickly become out of control, and they both knew something would need to be done, and soon.

_Once_ Jaune was sure his teammates were gone he quickly dressed. No doubt they'd be back soon enough and he would rather be alone. It wouldn't be hard to find a secluded spot, Beacon was quite large after all. He didn't mind if it took a while to find a suitable spot, the walk might help clear his thoughts.

It only took twenty minutes to find a spot removed enough from everyone, but walking had done his thoughts no good. Jaune decided the tree would make the best spot to sit, and slid down, resting his back against it's trunk. He closed his eyes. What did it all mean? She had ran from him. What did it mean? Did she not love him too? Had he been too hasty? What if he had screwed it all up? He sighed.

"I don't know what to think. Did I screw it up? Did I even do the right thing?"

"The issue with talking to trees, Mr. Arc, is that while they are tremendous listeners, they do not often offer much in the way of advice."

Jaune opened his eyes, surprised to see Professor Ozpin standing above him. The knight quickly shot up, giving the headmaster a courteous bow. Ozpin continued.

"There are many who think actions ought to be judged by their consequences. The trick to this is that consequences complicated, they are often hard to understand, and harder to predict.. They can be far reaching, and they may change over time. To know if something was the right thing to do you must consider it all." Ozpin smiled, his words seemed to have the desired affect, Jaune had a pensive look on his face. "Think of that what you will. I must be going now, farewell Mr. Arc."

"Thank you." Jaune said. Ozpin nodded politely in response before taking a sip from his mug and continuing walking.

Jaune had been given a lot to think about. There was more to this than what he was dwelling on.

_The_ dorm of team RWBY was silent. The curtains were drawn leaving the room dark. To any observer the room would seem empty. This was not in fact the case. A small figure lay on a haphazard bunk bed. She lay wrapped in blankets, staring at the ceiling. Ruby wasn't taking the end of the previous night that well. After her fleeing Jaune's confession she was sure he must hate her. And she was also convinced it was her fault.

In truth she hadn't really thought too much if she loved Jaune. At least not before last night. She thought about it now. Ruby couldn't say she knew what romantic love felt like, but she did know a few things. Jaune made her happy. He was nice and funny, and a bit of a dork. He was clumsy and got air sick, and sometimes was too hard on himself. But she wouldn't change anything about him. The more she thought the more clear it became. She loved him. Ruby Rose loves Jaune Arc. But she had spurned his confession. Her heart sank.

But only for a moment. Ruby was nothing if not persistent, and wasn't one to go down without a fight. She wouldn't let this hold her back. But she couldn't just rush into this without thought. She jumped down from the bed and pulled the blinds open. This called for a plan.

**Hey guys and gals, Theeubernoob here. This chapter is pretty light on the fluff, so sorry about that, but I feel it was important in the grand scheme of things. The next chapter should be a little longer, this one was mainly set up for it. Hope you like it, and as always your reading and or reviewing is appreciated.**

Up Next: The Three Plans


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